Urea → HCID 54101854, compound

HRID 1284187Notes

Reaction equation

HRID 1284187 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][CH3:12])=[O:10].C(=O)(O)[O-].[Na+].[CH3:18][S:19][CH2:20]Cl.NC(N)=O>CC(C)=O>[CH3:12][N:11]([CH2:18][S:19][CH3:20])[C:9]([NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])=[O:10]

Participants

6

Reactant 4

HCID 1176UreaHCID 16916Chloromethyl methyl sulfideHCID 516892Sodium BicarbonateHCID 676515N-(2-fluorophenyl)-N'-methylurea

Product 1

HCID 54101854HCID 54101854, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred slurry of 16.8 g. (0.1 mol) of N-(2-fluorophenyl)-N'-methyl urea, dissolved in 500 ml. of acetone containing 9.24 g. (0.11 mol) of sodium bicarbonate was added 10.6 g. ((0.11 mol) of chloromethyl methyl sulfide. The resulting mixture was stirred for 2 hours at a gentle reflux. The precipitated solid was removed by filtration. The filtrate was evaporated to give a clear oil. Crystallization from benzene gave 7.1 g. of the original urea. The filtrate from this crystallization was evaporated and the residue crystallized from diethylether to give 3.4 g. of a crystalline solid product, melting point 81°-82°C. Analysis calculated for C10H13FN2OS: S, 14.03%; F, 8.32%. Found: S, 14.02%; F, 8.43%. The infrared spectrum showed strong adsorption at 3.0, 6.9, 7.3 and 13.0μ. The NMR spectra was consistent with the assigned structure.

Workup

  1. customThe precipitated solid was removed by filtration
  2. customThe filtrate was evaporated
  3. customto give a clear oil
  4. customCrystallization from benzene
  5. customgave 7.1 g
  6. customThe filtrate from this crystallization
  7. customwas evaporated
  8. customthe residue crystallized from diethylether
  9. customto give 3.4 g

Sources & evidence

ORD record
ord-5c2fda54d1164f2a992d4ba1d54229bd
Source dataset
uspto-grants-1976_08
Patent number
US03978123

Reaction notes

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